| Saturday 2nd August 2003 | |||
| First Round | |||
| Airdrie United | 2-0 | Montrose | |
| Albion Rovers | 1-0 | East Fife | |
| Alloa Athletic | 1-2 | Clyde | |
| Ayr United | 1-2 | Stirling Albion | aet |
| Brechin City | 1-0 | Falkirk | |
| Cowdenbeath | 1-2 | Ross County | |
| East Stirlingshire | 2-5 | Raith Rovers | |
| Forfar Athletic | 4-0 | Elgin City | |
| Gretna | 0-5 | Inverness CT | |
| Hamilton Academical | 2-3 | St Johnstone | aet |
| Morton | 4-3 | Arbroath | |
| St Mirren | 3-2 | Queen's Park | aet |
| Stenhousemuir | 0-3 | Peterhead | |
| Stranraer | 2-1 | Queen of the South | |
» Scottish Challenge Cup 2003-2004 : Results
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